Microbiologic oxidation of estratrienes and estratetraenes by Streptomyces roseochromogenes ATCC 13400.
Incubation of estrone (1a) with Streptomyces roseochromogenes ATCC 13400 yielded a mixture of 3,16 alpha-dihydroxyestra-1,3,5(10)-trien-17-one (3a) and 3,17 beta-dihydroxyestra-1,3,5(10)-trien-16-one (4a). Transformation of 3-methoxyestra-1,3,5(10)-trien-17-one (1b), 3-hydroxyestra-1,3,5(10),9(11)-tetraen-17-one (2a), and 3-methoxyestra-1,3,5(10),9(11)-tetraen-17-one (2b) with the same microorganism gave the corresponding mixtures of 16 alpha-hydroxy-17-ketones and 17 beta-hydroxy-16-ketones (3b and 4b, 6a and 7a, 6b and 7b, respectively). In addition, in these three last experiments, the 16 beta-17 beta-dihydroxy derivatives 5b, 8a, and 8b, respectively, were also isolated. The complete assignments of the 13C nuclear magnetic resonance spectra of these compounds are given.
Ferrer
J C
JC
Department of Organic Chemistry, C.E.T.S. Institut Químic de Sarrià, Barcelona, Spain.
Calzada
V
V
Bonet
J J
JJ
D004963:Estrenes / Q000378:metabolism*; D004970:Estrone / Q000378:metabolism*; D005285:Fermentation / Q000502:physiology; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013302:Streptomyces / Q000378:metabolism*
D004963:Estrenes; D004970:Estrone